


I Can't Believe I Still Get Like This

by orphan_account



Category: Will & Grace
Genre: Confessions, Fluff and Smut, Love Confessions, M/M, Porn With Plot, Romance, Shameless Smut, Smut, Switching, Unrequited Crush, Unrequited Love
Language: English
Status: Completed
Published: 2018-10-19
Updated: 2018-10-19
Packaged: 2019-08-04 11:46:22
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,754
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16346120
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: Will starts noticing Jack a little too much. It isn't love. Is it?





	I Can't Believe I Still Get Like This

Will woke up to the sound of a pounding on the door. Or was that in his head? With a groan, he rose to his feet, running a hand through his dark hair and rubbing the sleep from his eyes. Before Will could even get to the door, the culprit of the horrendous noise marched through the door themselves, flailing their arm's dramatically.

"Will! Will Truman! Mr. Truman! You will never believe the most amazing bestest thing EVER just happened to me, you'll never guess, go on, guess guess guess!" As Will attempted to even process the screeching that had just come out of his friend's mouth, then he might be able to answer his question.

"Please, Jack, speak at a level that not just dogs can hear? I'd like to attempt to have a decent conversation with you for once, if that's not too hard for you to accomplish."

Jack scoffed and rolled his eyes. "Oh please! Stop being such a sissy and just guess!" He put his hand on one hip as he dramatically jutted it out to the side.

"Sissy? I don't think I'm the one most qualified for that title here now am I Jack?" Will raised a single eyebrow, a knowing smile starting to form across his face.

"Of course not! We all know I'm the best candidate. But that's not the subject here, now are you gonna guess what happened or not?!" Jack frowned, crossing his arms.

"Wait, don't tell me, you had a threesome with those two Brazilian twins that live on the fourth floor?" Will teased.

"No! You silly. That's just an added bonus." Jack giggled, lightly shoving Will's chest. "Now guess for real."

Will shook his head. "Damn, I'm all out of guesses!" He grinned as Jack pushed him again.

"Alright, alright you dummy, I won that drawing I entered online and got a free dinner at a nice restaurant for two! It's gonna be fantabulous! I'm bringing Javier."

"Well good for you, I hope you have fun." Will patted Jack on the shoulder, who turned to leave, but quickly turned back around.

"Wait a second, Will, can I have some cash for a gift for Javier? Obviously just a romantic dinner won't be enough, I'm telling you Will, this man is the one!"

"So you've said about the three other men you already went out with this morning." Will joked.

"Oh come on Will, please?" Jack batted his eyes, as if that would make any difference.

"Alright, fine. Here." With a sigh, Will pulled out his wallet and handed Jack a 50.

"Yay!! Thanks Will, you're the best! Okay, can't talk anymore, I've got a present to buy and a man to catch! Toodles!" With a final wave, Jack pranced out the door, running straight into Grace as he passed.

"Jeez, someone's feeling gay and dancey today." Grace huffed, fixing her red curls back into place. "Wait, who am I kidding, he's exactly that gay every day."

"Hi Grace, what brings you here today?" Will asked, closing the door behind his friend.

"Well, if you must know-"

"And you know I must" Will interrupted.

"Yes I know- Karen wanted me to come ask you for some of your alcohol, apparently she's having a crisis and can't get alcohol anywhere and-"

"She told people she was quitting didn't she."

"...Yes."

"Well if she's that desperate..." Will paused.

"Really?"

"No. Tell her to go out and get her own booze, like she's been doing since she was twelve. There can't be any more shame in it now than there was back then." Will smirked.

"Yeah okay, you're totally right about that one." Grace patted Will's arm. "I'll break the bad news to Karen if she comes to work today. She's been feeling extra flakey lately." Grace flopped down on the couch, snatching a cracker off the tray on the coffee table. " So, what's got Jack feeling so theatrical this early in the morning?" Grace asked through her cracker.

"Oh he won a dinner online and he's going to indulge in it with his new foreign boy toy. Plus I actually gave him cash today, surprising, believe me, I know! I'm the one who gave him the money!" Will waved his arms in the air for emphasis.

" Well, hopefully this pays off and he won't come back for more money." After a moment of silence, they burst out laughing. As if Jack would ever stop asking for money.

"Yeah right!" Will chuckled. "He's as bad as a lazy 12 year old who thinks he actually deserves his allowance." The laughter lasted a few more moments.

"Hey! Speaking of dates, I haven't heard anything from the romantic side of Will's personal life, have you seen anyone lately?" Grace cheekily leaned her chin on her hands.

Will sighed, looking away. "No. I haven't had any luck. I'm as lonely as ever. And I'm starting to think it's because of me..." Will looked down at the floor... " And not just because all the guys I like are too stupid to want to date me. Gracie... Maybe there really is something wrong with me?"

"Honey you know that's not true!" Grace stood up to give Will a reassuring pat on the arm. "You're a catch and any man or woman on the planet would be lucky to have you!"

"You really mean it Gracie?"

"Of course I do, Will. And I know you'll find someone to love you for who you are." Grace pulled Will into a warm embrace.

"I'm not getting any younger though, Gracie. I just hope I won't have to wait much longer."

"And I better not keep Karen waiting much longer or I'm afraid of what she'll do to me and my office." Grace pulled out of the hug with a pat on Will's back and sneakily grabbed a bottle of gin for Karen.

"Alright. I'll see you later Gracie. Love you."

"Love you too, Will." Grace shut the door behind her, leaving Will alone with his thoughts.

...

"Jacky that's wonderful! I'm so happy for you poodle!" Karen squealed from her seat.

"What's happening?" Grace asked, shutting the door behind herself.

"Oh nothing honey, just congratulating Jack on getting Will to cough up money for his date tonight!" Karen replied, turning from her nails painting position to address Grace. "It's not easy to get that boy to do anythi- ooh you got the booze!" Karen stopped her monologue and snatched the bottle of gin from Grace's hands.

"Oh yeah, and you'd better be grateful cuz I swiped that for you this morning." Grace set her bag down on her sketch table. "If I said it wasn't easy though, I'd be lying, so maybe I'll only make you do a little bit of work today."

"Um, hellooo~ I'm here too?" Jack waved his fingers in front of Grace's eyes. "Aren't you gonna say hello to me Gracie?" Jack pushed.

"Only if you wanna work for me today too, you gay money snatching weasel." Grace teased.

"No m'am! I've got a life to live! Gooooodbye!" Jack turned on his heel, waving with the 50 dollar bill as he left the office.

...

Will sat in his office the rest of that day, stamping files worth of papers for clients as usual, nothing exciting or interesting taking place throughout the entire afternoon. The silence only accentuated the feeling of being alone.

"Man.. I thought I liked the quiet until now." Will said to himself, running his hand through his hair in boredom. He could hear every sound. The ticking of the wall clock, the sound of the pigeons outside his window, the footsteps of co-workers as they passed by his office... Yet no one came in to greet him that day.

He hadn't even gotten a call from Grace that afternoon. Hell, he'd even settle for Jack or Karen to call with a simple hello or a story about their day so far. Yet there was nothing. No messages on the machine and not a call in sight.

Will sighed softly. Maybe he should go out... Reluctantly, Will pulled a small notebook out of his top desk drawer and flipped through several pages phone numbers. But none of them jumped out to him. None of those people would care to talk to him. They would all surely be busy with their own lives at this point.

Will looked at his watch. At least it was almost time to get off work already. He could go home and spend the rest of his evening watching a movie and eating until he fell asleep. That had become his reality more and more regularly. Ever since he had decided that he wasn't good enough for anybody. And today, well he sure as hell felt unwanted.

As much as Will wanted to push that feeling away, he just couldn't. With a sigh, he got up from his desk to head home.

...

Pushing open his door tiredly, Will entered his apartment, kicked off his shoes, and grabbed some leftover lasagna from his refrigerator. He heated the day old food in the microwave. It came out half crunchy and only lukewarm.

"Huh. You remind me of myself, you sad, crunchy, reheated pasta casserole. You have so many layers and none of them are hot anymore." Will took a bite. "Yep. Delicious."

He loosened his tie and pulled it over his head, throwing it over a dining chair. Despite usually being organized, Will didn't quite feel like it today. He threw himself down on the couch in front of the TV, ready to spend another night alone. Will hated how he felt. He hated being alone. And he hated being so used to it.

Was Grace really right? Would Will ever find someone to love him for him? He doubted it. Why else would he still be alone? He was gay. And in his 30's . It was basically a sign that maybe he would never be able to find someone? Will hated feeling like it was too late for himself.

He rubbed his eyes, no longer paying attention to the movie. How could he when he was watching it alone?

Just then came a soft knock on the door, startling Will. Who could it be at this time of night? It was already 10:30, Will was surprised he himself hadn't fallen asleep already, so who else could possibly be awake to come visit him?

Opening the door, he was greeted by a soft frown on Jack's face, his eyebrows furrowed and the corners of his lips turned downward slightly.

"Jack? What are you doing here? Shouldn't you be out enjoying your date with Javier?"

"Yeah. I was supposed to." Jack walked in past Will and took a seat on the front couch. "But instead I'm here to return this." Jack pulled a 50 dollar bill out of his pocket and handed it to Will.

Confused, Will didn't reach out for the money. "Wait, Jack. What happened? You never return money you've borrowed."

"Very funny Will, but now isn't the time for standup. Just take your money back." Jack didn't look Will in the eye, but pushed the money toward him until Will took it from his hand.

"Okay, but why would you need to do that?"

"Why do you think, Einstein! It's because Javier blew me off! He didn't show up for dinner..." Jack looked down at the floor, his hands folded solemnly in his lap.

"Wait. You? You got blown off? How? And why?!" Will leaned on the table, his arms crossed.

Jack shrugged weakly. "I don't know. No one has ever done that to me before. It feels awful."

Slowly, Will placed his hand on Jack's shoulder. "I'm so sorry Jack. I know how bad a feeling it is to get stood up. It's me you're talking to you know!" Will attempted to make the situation less heavy.

"Yeah. Thanks Will." Jack sniffed, wiping the corner of his eye. "You know your misery always makes me feel better."

"Wait? What do you mean by that?" Will frowned. Jack chuckled a little bit

"I was kidding. It only sometimes makes me feel better."

"Hey! Rude!"

"Heheh, sorry Will."

The silence lasted a few moments.

"So, I'm watching a movie by myself right now. Wanna come join me and make it both of us watching TV alone?" Will gestured towards the TV room.

"Yeah. Let's go be by ourselves together. I wouldn't want you to be alone all on your own." Jack smiled, offering Will his arm. Will smiled and took it, walking them to the TV room to be alone together.

...

When will woke up, he could feel the soft weight of another body on his own. As the sleep left his eyes, the form of Jack's face took shape in front of Will. His cheek was pressed against Will's chest, his mouth open slightly as he drew soft breaths, his eyebrows relaxed and his eyes were lightly closed.  
  
Will swore he had never seen Jack look so peaceful. So innocent and gentle. His face was illuminated in the blue-ish glow of dawn light just barely cutting through the blinds. He almost looked- ... beautiful. As he reached up to gently touch Jack's hair, he stopped himself. What was he thinking?

"Hey. Jack get up." He said quietly. When Jack didn't stir, Will debated falling back asleep, but his better judgement voted against it. "Jack!" He said louder, shaking his friend's shoulder. "Hey! Get up!" Will sat up, finally waking Jack, who slowly leaned up and stretched his arms in the air, his shirt sliding up revealing the smallest bit of his stomach and hips.

Will turned his head away, feeling suddenly self conscious. He didn't know why. He had seen Jack shirtless plenty of times. Why would now be different? Will shook his head, not wanting to dwell on that any longer.

Jack stood up, yawning loudly before making his way to the kitchen.

"So, what's for breakfast?" He called to Will sleepily.

"There are still some Eggo's in the freezer if you want that." Will suggested, getting off the couch as well. He joined Jack in the kitchen to make some coffee. "Jack, I gotta get by you to make coffe-...!" Before Will could finish his sentence, Jack had grabbed his waist and quickly switched their places.

"There ya go, perk away!" Jack said cheerfully. Will swallowed. What was wrong with him? He was noticing everything Jack was doing. Every movement was so accentuated in his mind. Will shook his head, trying to get rid of the awareness. Maybe he was just still tired...

...

The two of them sat quietly eating their breakfast, Will was trying to concentrate on reading his newspaper, but Jack kept catching his eye. The movement of his arm from his plate to his mouth was so distracting. Will didn't notice himself staring until Jack looked up at him.

"What's up with you this morning Will? Jack asked, tilting his head to one side. "you've been weird ever since we woke up. Are you feeling okay?" Jack stood up and leaned across the table, ready to put his palm across Will's forhead to check for fever. Quickly, Will grabbed Jack's wrist, stopping him.

"No! Jack, don't touch me." Will blurted out.

"What the hell is wrong with you Will! You're acting like you've just come down with some sort of disease or something!" Jack gasped. "Wait, you haven't, have you?!"

Will let go of Jack's arm and looked away, slightly embarrassed. "No! Of course not, you moron." He huffed, brushing his hands off on his shirt.

"Well, what the Dickens is it then, you silly man?" Jack crossed his own arms.

"I-" Will looked down. "I don't actually know. It's just weird. I'm weird..." Will pushed his chair in and took his plate to the sink, not looking at his friend directly.

"C'mon Will, we've been best friends forever, you can tell me what's wrong."

"That's the thing, Jack! I don't know what's wrong with me! If I knew im sure I would tell you! So until I figure out what's wrong with me, I won't be able to tell you!" Will frantically washed his plate, his fingertips burning from scrubbing so hard.

They were both quiet for a long time.

"Well.. I guess if we have nothing else to talk about, then I can just go. I'll see you later then Will. Call me if you need to talk. I may or may not be there to talk to you. Just take the chance." Without waiting for a response from Will, Jack turned and left, closing the door quietly behind him, leaving Will to do the dishes in silence.

...

"See, Grace I don't know what to do! I don't even know what's going on with me!" Will ranted to his red headed friend who was sitting in the office chair in front of his desk. She was listening intently, occasionally pausing to take a sip of her mocha in hand.

"It's just, everything Jack did was like it was magnified or intensified I something like that! You know what I mean it was just so... There! It was happening right in front of me! I've never noticed things like that before, not about Jack anyways, so... I'm really confused. I think I might be sick or something. What do you think?" By the time Will finally stopped talking, he noticed a knowing look spreading across Grace's face.

"Grace, what is that look about?"

Grace's smile only widened.

"Will... I need you to think for a second. When were any other times that you can think of where something like this happened to you before? You may need to think back. To people in your past maybe?" Grace sipped wisely on her coffee.

"Gracie I don't see where you're going with this I-"

"Think about it!"

"Okay, okay!" Will threw up his hands in mock self defence. "Um.. I don't know, I guess the last time this happened was when I liked Barry... "

"Uh huh... And...?"

"I don't know, maybe also when I met Paul?"

"Okay... And?" Grace pushed.

"And what?"

"Oh come on Will! Think! Do I have to spell it out for you? What did both of those people have in common with each other?"

Will thought for a moment.

"They're both men?" He shrugged. "Really, where are you going with this Gracie, I don't get it."

"Yes! Men, Will! They're men! And what does that mean to you?!" Grace was practically shouting at him now, also she was halfway to climbing up on the desk.

"Jesus, Grace, I guess... I like men? Still I don't understand what this would have to do with-" Will gasped, covering his mouth.

"Fucking finally, Will! Good God, I really had to do everything but spell it out for you huh?! You would think that you would have gotten it by now considering that you're smart and all but I guess not! So what-" Will stopped Grace from speaking anymore.

"No. Gracie. That can't be it. That's impossible. Jack is one of my closest friends. I could never think of him in that way."

Grace raised an eyebrow. "Will. Honey. You looked at his stomach when he stretched in front of you. I don't think it could get much more obvious than that."

Will stopped fighting with her.

"Grace... Do you-?" He took a deep breath. "Do you really think so?" Grace nodded slowly.

"Yes Will. I do. He's your closest male friend. How could you not think of him that way at least once in your life? It will pass if you let it you just-"

"Gracie. What if this has been going on forever, but I haven't acknowledged it because I'm afraid?"

Grace didn't respond, she thought for a long while, struggling with what to say next.

"Will... Is that true? How long have you felt this way?"

"I don't know... I think it's just been this way ever since I met him back in college..."

"Oh sweetie... I don't know what to say..."

"Yeah. I don't either. I guess I'm just surprised most of all..."

"Well..." Grace held both of Will's hands in her own and looked into his eyes. "It must be because you've been alone. You're experiencing a lack in romantic closeness and if you really have felt that way about Jack... Then the feeling would come back when you're alone. And Jack is always there for you." Grace took a long breath. "Will. I think you need to tell him. Jack needs to know what you're thinking right now."

"But-"

"Sorry Will. No buts. He's your best friend. He deserves to know what you're feeling right now. No matter how you decide to tell him."

Will frowned, unsure of what to say.

"I... I guess I do need to tell him. Thanks Grace. You always know what to say. I don't know how I'd live without you. And... I don't know how I'd live without Jack. I'll talk to him tonight. You can trust me on that."

Grace smiled and patted Will's hand gently.

"Good. You need this. Jack needs this. Open up to him Will. You night be surprised at what comes out of it."

"I'm so afraid, Gracie. I don't want to ruin my friendship with him.. something like this could tear us apart you know..."

"Yeah. I know." Grace pulled Will into a hug. "But I know that the risk is worth it." She whispered in his ear. "We dated for a long time and look at us now! Everything between us turned out fine. So why are you hesitating so much to take that chance with Jack? You're wasting your time by being afraid. If you and Jack are really as close of friends as you say, then this won't hurt you guys. Believe me. I know."

Will hugged Grace tighter.

"Yeah. I know. Love you Grace. Thank you so much. For everything."  
  
Grace pulled apart from Will and smiled. "You're welcome. And I love you too. Now go get him tiger."

...

That evening, Will was so nervous. He had called Jack, who reluctantly answered and agreed to coming over for dinner at Will's apartment. Which really wasn't too much of a feat since they lived right across the hall from one another.

Will wringed his hands together as he moved the dishes back and forth, trying to decide whether or not they were in good enough spots.

"No. Will. It's fine. Calm down." Will shook his head to attempt to rid himself of the butterflies he was getting. But the nervous feeling stayed.

Will looked at his watch. It was already 5 minutes past eight. Where the hell was Jack? He felt himself unwillingly tap his toe, his own fidgeting was starting to drive him into a state of worse nervousness. He knew Jack would be there soon. Right?

After a few more painfully slow minutes in silence, the doorknob clicked and Jack entered the room, a familiar stiffness in his walk that signified his irritation.

"Jack... Um hi. Please don't tell me you're still mad?" Will asked, continuing to wring his hands in his lap.

"I don't know Will." Jack said harshly, avoiding Will's gaze. "Are you still a jerk?

"Jack, im-"

"Good. I hoped not. Now what's for dinner?" Jack suddenly plopped down in the chair across from Will, casually adjusting the plate and putting a napkin into his lap. "I'm hungry. And I know what you made is gonna be good. It always is."

"Oh... Well. Thanks Jack, it means a lot to me to hear you say that. Thank you."

"You're welcome." Jack nodded once.

Will got up and walked into the kitchen grabbing the tray of chicken that he had taken out of the oven shortly before Jack had arrived.

"Hope you don't mind this chicken not being fried." Will joked, placing the platter on the table before cutting off a piece to put on Jack's plate, and then his own.

"So..." Will cleared his throat. "Jack, this is hard for me to say.. but, you know, I'm really sorry about how I acted this morning. I was really cold to you. And I had no reason to be." Will awkwardly avoided looking at Jack's face.

Jack listened intently as he took small bites of his meal, Nodding as Will spoke slowly.

"Really Will, you know it's fine. I don't take things like that too seriously. I mean, sure it hurt my feelings in the moment, but I'm really sure you had your reasons for being cold. And you really don't have to justify that to me-"

"No, Jack. I do have to justify it." Will interrupted his friend, swallowing his nerves before speaking again. "And yeah, I did have my reasons. But no reason that should have caused me to distance myself. What I have to say is really important, Jack, so please listen." Will took a shaky breath, his hands trembling slightly as he held tightly to his glass.

"Jack... I think I might have feelings for you."

Jack stood up quickly.

"Will, I knew you would do this to me!" He shouted. "How dare you even suggest I have feelings for you! Why I would never even-!" Jack paused, his eyes wide as he looked at Will. "Wait. What?"

Will stayed quiet, though he had moved his gaze up to meet Jack's.

"I'm not hallucinating right?" Jack chuckled softly, sounding somewhat panicked.

Timidly, Will shook his head. His shaky grasp not loosening on his water glass.

Slowly, Jack sat back down, raising his arm to place his palm across his forehead. "Will I-" Jack's eyebrows furrowed in obvious confusion. "Will I don't understand. What-?" Jack didn't finish his sentence. But he didn't need to.

"No, Jack, it's okay. I understand your confusion. This is super sudden and all, trust me, I know. As for what caused this?" Will felt himself letting go of his shyness. "I think it's because I'm alone, Jack. I'm alone and the only guy who has always been there to help me through is you. And I guess... I guess I just wanted to be able to do the same for you... And it made me start thinking about how many times you've dumped guys and how many have dumped you. And you always seemed so unfazed... So I guess in my mind I just assumed that even though I needed you... That you really never needed me." Will let out a deep breath before looking up to see Jack's face.

"Wow. Will, I- I never had any idea." Jack's expression was still currently a mix between shock and confusion. "I don't know what to say..."

Will swallowed nervously. He could practically see Jack trying to decide what to say next.

"Will. I'm really not as strong as you think I am. Every single breakup... It doesn't just tear me apart, Will. It also makes me realize how little I care about all the men I've been with. Honestly Will... I'm awful. And I'm not resilient." Jack ran his hand through his hair with a sigh. "Will, I don't like dating so many people all the time. It's just all I can do to not think about my feelings for you."

"Wow..." Will absorbed all of Jack's words.

"Ever since you rejected me back in college... The hundreds of guys that I've dated and thrown away... None of them ever lived up to what my friendship with you is. Even with all the sex. No one matters to me as much as you do Will." By the end of Jack's speech, his shoulders we're shaking and there were tears streaming down his face. Will's heart skipped.

"Jack, please, don't cry." Will stood up, quickly pulling his friend into a tight embrace. "I was supposed to be the one confessing here. I feel awful. I didn't know you felt that way about me for so long."

Jack wrapped his arms tightly around Will's shoulders, sobbing against His neck. "Oh Will... I could never get you out of my mind... I could never forget when I met you, I immediately knew that you were the one I wanted in my life. I was only in my senior year of high school, but that didn't matter to me. You were perfect. And you still are." Will softly rubbed Jack's back listening to his friend pour out his emotions.

"Jack... I'm so sorry. Back then... How was I supposed to know that we would get to this point? I'm so glad we became friends instead of dating. I would have hated if we had to break it off. Jack... I'm so afraid if ever starting a relationship with you. But only because I desperately would want to keep it forever. If I had you... I would never want to let you go."

"You mean it?" Jack pulled apart third embrace to look into Will's eyes. Will nodded with a soft smile.

"Yes Jack. I mean it." Jack looked down at the floor, the two stood there, silent, with just the soft sound of their labored breathing. Jack looked very afraid, but also sure as he raised his head again and slowly pulled Will's face toward his own.

"Jack, I-"

"Shh.." Jack put his forehead gently against Will's. "It's too late for you now." Jack spoke quietly. "We both told each other all we need to know, so just shush your trap and let this happen like it's supposed to." Jack pushed his mouth softly against Will's. It wasn't the first time they had ever kissed, but Will couldn't help but notice that it felt like Jack had no clue what he was doing.

"Jack. Hey." Will pulled his face away from Jack's, who gave him a self conscious glare.

"Oh don't say anything, Truman..." Jack huffed, his face slightly flushed with embarrassment. "This is just weird you know. I never actually thought that this would happen."

Will smiled softly, rubbing his finger over Jack's forehead to stop him from frowning. "Shh... It's all right Jack." Will placed his hand on the back of Jack's neck, gently teasing the close cropped hair underneath his fingertips before pulling Jack's mouth back against his own, this time, taking control and gently leaning Jack's shoulders against the wall. This time when their lips separated, it was for Jack to take a breath, his eyebrows furrowed again as he looked away from Will, the flush across his face slightly darker than before. Will raised his hand up to Jack's face and lightly brushed his fingers across the skin from his right ear to his jaw, causing Jack to draw a shaky breath.

"You're so pale." Will said in a hushed voice. When Jack opened his mouth to debate, Will interrupted. "It's beautiful." Jack closed his mouth again, only to have Will suddenly pull Jack's face back up to his own, quickly locking their mouths together again, this time, Will forcing entry with his tongue, holding the back of Jack's neck firmly, pulling him closer. Jack made a small noise, surprising Will into breaking the kiss. Jack was breathing heavily now, his hands fisted into Will's shirt, his brows still deeply furrowed.

"Jack? What was that about?" Will breathed, still a little shocked at their sudden intimacy.

Jack shook his head. "I-... I dunno." He moved his gaze to meet Will's. "Just do it again." Not taking another second to consider it, Will pushed Jack up against the wall with his hands against his hips, moving his mouth hungrily against Jack's, the two of them both fighting for control against the other's tongue. Will won, but he guessed it was because Jack wanted him to. After a few moments, Will noticed that Jack was trembling, small tremors running up his body with every kiss. Curiously, he snuck his hands under the hem of Jack's sweater and button up, and gently caressed the bare skin of Jack's stomach.

Jack let out a sharp moan and a visible shiver traveled up his body, his hips suddenly pressing into Will's as a jolt.

Will's eyes widened in surprise. He had expected some kind of reaction... But nothing that intense already.

"Jack, what-"

"Will... Please! Touch me again" Jack grabbed Will's hands and led them up under his shirt, directing both of his palms across Jack's soft skin. Will could feel the constant tiny shivers running across Jack's body. He swallowed, watching Jack's chest rise and fall dramatically with his breath, feeling his ribs expand and contract with every soft sigh that was leaving his mouth. Will took a deep breath and took his hands off of Jack, who started to whine softly.

"Sh-h.." Will hushed him and grabbed the hem of Jack's sweater, pulling it up over his head and tossing it aside before moving to unbutton his shirt, his fingers trembling as he moved down until Jack's torso was visible underneath. Sliding Jack's shirt off of his shoulders, Will exhaled nervously.

"Wow..." he breathed out, looking over Jack's smooth white skin until his eyes came to rest on Jack's soft pink nipples, already slightly swollen whether from the cold or arousal, but Will couldn't tell. Not like it mattered. He laid his hands once again on Jack's toned stomach, feeling him let out a quick rush of breath.

"Will... Your hands, they're really hot." Jack muttered. "You're not nervous are you?" He teased. Will flashed him a glare before quickly running his hands up Jack's body.

"Oh yeah? Says the guy trembling like a virgin." Without warning, Will licked his fingers and pinched Jack's left nipple. Jack let out a high pitched yelp, his back arching as a violent tremor shook his body. Will watched Jack's every reaction closely through now half lidded eyes, his teeth clamping down softly on his own tongue.

"Fuck... What's wrong with me today..." Jack whined as Will relentlessly rolled his nipple between his slick fingers.

"Did you just curse?" Will whispered to himself curiously, before leaning in and breathing softly against Jack's chest, slowly closing his mouth over his other nipple.

"Ah! Fuck! Will!-mn!" Will interrupted Jack's moans by kissing him again, their tongues moving feverishly with each other. Jack pushed Will off of him after what seemed like minutes, his breathing frantic and heavy. After they caught their breath and regained control of themselves, Jack slowly took Will back into his arms and pulled one of Will's thighs between his own. He rested his chin gently on Will's shoulder and whined breathily against his ear as he thrusted slowly against Will's thigh.

Will closed his eyes tight and listened to the sound of Jack's uneven breath, the quiet moan integrated into each one that went along with every delicate thrust that was dragged against his leg. His own pants were already unbearably tight, though he didn't even remember when it had gotten that way. Will shifted his leg under Jack's groin, who's breath hitched as he let out a loud moan, his knees buckling beneath him.

"Whoa!" Will caught a trembling Jack in his arms. "God, Jack. You're so sensitive..." He ran his fingers delicately against Jack's lower back, watching the muscle shiver underneath the skin.

Jack hissed through a moan. "I'm never like this.. Mmn! I don't know what's wrong with me tonight..." Will stopped drawing circles on Jack's skin, his own face flaring up red in realization.

"Jack..." Will swallowed. "It couldn't be because it's me touching you... Right?" Will didn't want to make this all about himself but somehow...

Jack's eyes widened, a dark blush spreading across his cheeks.

"Thought so." Will put his arms under Jack, who shrieked in surprise, and lifted him before quickly walking to his room and throwing Jack down onto the bed. He pulled his t shirt over his head and leaned on the bed over Jack's body, kissing him like he owned him. With one hand, he fumbled with Jack's belt, the buckle clinking as it slid off of him. With the other, Will teased at one of his swollen nipples, Jack squirming in pleasure under him.   
Slowly, he managed to push Jack's jeans down off of his waist, revealing his underwear, his hard dick poking out of the top of the waistband, the tip already oozing precum. Will stopped to take a deep breath, almost not believing that this was really happening right now.

"C'mon... Will, stop staring and touch me already." Jack arched his back, his cock twitching in anticipation. Will swallowed his sudden nerves before reaching out with tentative fingers and gently touched Jack's tip, who pushed upwards with a whimper, pressing Will's fingertips harder against him. More precum dripped down the side of Jack's cock, coating the ends of Will's fingers with the shiny liquid.

He looked up at Jack, who was biting down on on his lip while watching Will's face, pinching his own nipple between wet fingers.

Will flinched as he felt his own cock twitch painfully against the inside of his pants, begging to be touched. Jack smirked knowingly before grinding his knee against Will's groin.

"Hey!" Will shouted, feeling his body react positively to Jack's touch.

"Well?" Jack cooed breathily, rubbing circles on Will's crotch with his knee. "Let him out~"

Will breathed deeply as he removed his own pants and underwear, letting his dick spring free, curving upwards to meet his stomach.

"Mmn.." Jack hummed happily, his own dick twitching in response to seeing Will's "Now we're getting somewhere." Jack sat up on his knees and crawled to the edge of the bed, where Will stood watching him. He wrapped his arms around Will, pulling their chests together and reaching between their hips to grab at both of their cocks, Will gasped, his head falling forward against Jack's shoulder. Jack gave a tiny chuckle before moving his hand, twisting his wrist with every tight pull. Will subconsciously nibbled on Jack's neck and shoulder, biting hard with every other stroke. Jack hissed in pleasure tilting his head to the side to allow Will more freedom with his mouth, kissing up and down Jack's neck shoulder and collarbone, leaving soft pink bite marks as he went.

"Mm.. Jack..." Will breathed. Jack's breath hitched at hearing his own name from Will's lips.

"God, Will you're so fucking cute." Jack chuckled against Will's ear, stroking both of them a little faster. He continued until Will's breathing sounded dangerously quick, and he abruptly let go, halting both of their orgasms before they could finish. With a thick breath, Will pulled back, looking confused.

"Why did you stop?"

Jack just smirked and opened Will's bedside drawer, taking out a bottle of lube.

"Hey! How did you know that was there!" Will asked, snatching the bottle from Jack's hands.

"Oh yknow snooping." Jack giggled. "Anyways, you gonna open it then?" Jack asked, running his fingertips up Will's arm. Will shivered lightly, but pretended not to notice.

"Yeah fine." He cracked open the bottle as Jack watched with a small smile, slowly stroking his own cock again.

Will fumbled with the bottle, knowing Jack was just trying to be an asshole and distract him. Well it wouldn't work. With a frown, Will coated his fingers in the sticky substance and warmed it up slightly before timidly moving his hand towards Jack's ass. Jack continued touching himself with a smirk as he watched Will struggle to build up enough confidence to place his finger over Jack's hole. Will breathed shakily and rubbed gentle circles across his ass. Jack let out a thick sigh and pulled his dick tighter, watching Will through lidded eyes. Not wanting to wait any longer, Jack, moved his hand down with Will's and pushed two of Will's fingers inside of himself, his eyes fluttering closed as he moved Will's hand. Slowly as he felt Will getting more confident, he removed his own hand and let Will loosen him up, enjoying the feeling of his fingers stirring him up. Jack opened his eyes when he felt Will stop and remove his fingers, and was surprised to see Will hanging over him, staring at Jack's face as he stroked himself, his eyes not focused on anything but Jack.

"Will?" Jack cooed, tilting his head to one side.

"Lift your legs." Will demanded, half out if it, pushing one of Jack's legs up himself. Jack complied, bending his knees up to his chest.

Will let out a soft growl as he looked up and down Jack's body, grabbing one of his knees before half timidly pressing his dick up against Jack.

"Mn~!" Jack's body shuddered as Will slowly pushed inside of him, his eyebrows furrowed intensely.

"Jack... You're so hot inside... Feels good..." Will mumbled sexual nonsense as he slowly pushed in and out of Jack, who was trembling again, every thrust bringing a soft whine from him. His dick was trapped between both of their torsos as Will moved, making Jack closer to cumming than before. He watched Will intently hearing Will moaning his name very softly under his breath. Soon after that, Will hit just the right spot, drawing a loud moan from Jack. Will's eyes fluttered open, and he pushed deeper into that one place, hitting Jack's prostate with every movement.

"Ah! Fuck!" Jack was close. But he could tell Will still wasn't quite there. After a few more moments of soaking in the surreal pleasure of Will slamming his prostate over and over, Jack forced himself to grab Will's hips.

"What..." Will mumbled, struggling to keep himself from continuing to pound into Jack.

"Shhh... Just go slower..." Jack whispered, then let go of Will's hips, allowing him to continue to slowly grind into him, digging deep into him in a softer way.

"That's it..." Without drawing Will's attention, Jack coated his own fingers in the lube. How could he forget that Will was a bottom as well? Jack ran his fingers over Will's ass once before pushing them inside, causing Will to stop and take in a surprised gasp, his hips suddenly pushing back into Jack's fingers, grinding them deeper inside him.

He let out a breathy moan, his eyes closed tight.

"Jack! Yes..." Will whined softly. He continued thrusting into Jack at a quicker pace, Jack keeping up by following him with his fingers. Soon Will was holding onto Jack tightly, moaning loudly against his ear for more. Jack felt a smile spread across his face. He sat up, leaning into Will's lap, who didn't stop moving and just continued to thrust upwards into Jack, riding into Jack's fingers as he moved.

"Mmn! Jack... Jack! Fuck!" Will and Jack's moans began to blend together as they continued to push into each other, Jack felt a familiar tightening in his groin and his head fell back, pushing himself hard down into Will and grinding himself there until he came across both of their chests, feeling Will nibble at his throat. As Jack came down off his high, he pushed Will down on his back and focused everything into grinding down and pushing in with his fingers until Will was moaning his name over and over, before finally cumming inside of Jack, his hair pushed back with sweat, his face flushed. Jack breathed deeply before pulling his fingers out of Will and getting off of him, only to fall down on the bed by his side. They both lay there, not speaking until they were both breathing softly again.

"Wow." Will muttered, almost as a sigh. Jack rolled over on his side and faced Will with a knowing smile. "Wasn't as bad as you thought it would be, huh?" Jack teased.

"Oh stop it." Will gave Jack a light slap on the arm. Jack giggled. "You're right though." Will sighed. "I really wasn't sure how that would go... Not just the sex. I didn't know if I would get through confessing to you and remain friends... It was a huge gamble." There was silence again for a short while.

"Me too. But I never imagined you would ever like me. I always just joked about it because I wanted it to be true. And now here we are. Covered in each other's semen."

"Jack!" Will slapped his arm again. Jack giggled.

"Will?"

"Yeah?"

"... I love you..."

Will looked into Jack's eyes with the smallest smile.

"I love you too, Jack."

....

  
Epilogue

  
"Congratulations you guys!!" Grace squealed as she pulled Will into a hug. "We could have never seen this coming!" She said to Will but mouthed "oh yes we did" at Jack over his shoulder.

"Oh yeah. Me neither." Will told her as he and Grace separated from their hug. " If you would have told me a week ago that I would be dating Jack, I would have told you to go to hell and see a therapist! Not in that order."

Karen finished giving Jack a tight hug of her own.

"Aw Poodle, I'm so happy for you two! I absolutely knew this would happen one day but what do you know! It actually did!"

"Thanks Kar! You totally get it!" He nodded at her dramatically.

"So what's gonna be the next part of this for you guys?" Grace asked, plopping down on the couch.

"Well, I was thinking we'd move Jack to here from his apartment across the hall." Will said, pouring himself a cup of coffee.

"You don't think it's a little too soon?" Grace asked.

"Well, no not really. We've already been best friends for basically ever, what would we need to get used to now that we're dating?"

Grace, Karen, and Jack all raised an eyebrow.

"What!?" Will crossed his arms.

"Well, the fucking, obviously." Karen shrugged.

Will spit out his mouth full of coffee.

"Yeah Will! What we did last night was the first but not the last time it's gonna happen!" Jack laughed, leaning against Will's shoulder.

"Oh please! If you do to me what you did last night every day, I'll be dead in a week!"

Karen and Grace both turned to face Jack, eyes open wide in surprise. Grace questioningly pointed at Jack, who nodded proudly, waggling his eyebrows.

"Wowww who would have known that Jack would be a top!"

Will spit out his coffee again.

"WHAT!?!" Will laughed out loud. Then stopped abruptly. "Y'know, I really wouldn't put it behind him."

**Author's Note:**

> Thanks for reading!
> 
> I adore these two, k thanks


End file.
